John Fitzsimons

Portside Real Estate Group

John Fitzsimons

Since 2013 I have had the opportunity to work on hundreds of transactions across the Greater Portland market, earning recognition as one of Maine’s top brokers. I specialize in expertly marketing and selling high‑end properties, using a tailored mix of sophisticated online exposure, targeted print, and a strategic network to maximize results for my sellers and find unique opportunities for my buyers. My deep market knowledge, inventory familiarity, and strong relationships with leading [...]

Since 2013 I have had the opportunity to work on hundreds of transactions across the Greater Portland market, earning recognition as one of Maine’s top brokers. I specialize in expertly marketing and selling high‑end properties, using a tailored mix of sophisticated online exposure, targeted print, and a strategic network to maximize results for my sellers and find unique opportunities for my buyers. My deep market knowledge, inventory familiarity, and strong relationships with leading local agents, builders, bankers, title companies, contractors, and tradespeople allow me to navigate each distinctive sale, whether a single‑family home, condo, multi‑unit, land, or luxury estate with confidence and precision.


Not all sales are created equal; my experience and ability to see the big picture provide clients with clarity and peace of mind throughout the process. Originally from New York and a Maine resident since 2010, I love the Greater Portland community—its restaurants, arts, music, and outdoor lifestyle. Outside of work I enjoy skiing, travel, running, exploring the coast, and the beaches with my wife Lindsey, our two boys James and Charlie, and our two black labs. My mission is to deliver exceptional service, measurable value, and a seamless real estate experience for every client.

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Hi there! How can we help you?

Contact us using the form below or give us a call.

Send Us A Message:

I agree to receive marketing and customer service calls and text messages from John Fitzsimons. To opt out, you can reply 'stop' at any time or click the unsubscribe link in the emails. Consent is not a condition of purchase. Msg/data rates may apply. Msg frequency varies. Privacy Policy.

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